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14-September-2008 18:02:45 - Dehydroepiandrosterone Redirected from DHEA Dehydroepiandrosterone Systematic IUPAC name 3-hydroxy-10,13-dimethyl -1,2,3,4,7,8,9,11,12,14,15,16 -dodecahydrocyclopenta aphenanthren-17-one Identifiers CAS number 53-43-0 ATC code A14AA07 PubChem 76 Chemical data Formula C19H28O2 Mol. mass 288.43 Physical data Melt. point 148.5 °C 299 °F Pharmacokinetic data Bioavailability ? Metabolism Hepatic Half life 12 hours Excretion Urinary:?% Therapeutic considerations Pregnancy cat. ? Legal status Commercially available US, Rx Only CA Routes Oral Dehydroepiandrosterone DHEA is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain and in the skin by an autocrine mechanism. DHEA is the precursor of androstenedione, which can undergo further conversion to produce the androgen testosterone and the estrogens estrone and estradiol. DHEA is also a potent sigma-1 agonist.1 Contents 1 Synonyms and brand names 2 Dehydroepiandrosterone sulfate 3 Production 4 Role 5 Effects and uses 5.1 Disputed effects 6 Increasing endogenous production 7 Legality 7.1 United States 7.2 Canada 8 References 9 External links Synonyms and brand names Synonyms for Dehydroepiandrosterone are: Dehydroisoandrosterone; 3β-Hydroxy-5-androsten-17-one; 3β-Hydroxyandrost-5-en-17-one; Dehydroisoandrosterone; Hydroxyandrost-5-en-17-one; Prasterone; trans-Dehydroandrosterone. Brand names for DHEA include Prastera, Fidelin and Fluasterone; supplement versions are manufactured from wild Mexican yam. Dehydroepiandrosterone sulfate Dehydroepiandrosterone sulfate DHEAS is the sulfated version of DHEA. This conversion is reversibly catalyzed by sulfotransferase SULT2A1 primarily in the adrenals, the liver, and small intestine. In the blood, most DHEA is found as DHEAS with levels that are about 300 times higher than those of free DHEA. Orally-ingested DHEA is converted to its sulfate when passing through intestines and liver. Whereas DHEA levels naturally reach their peak in the early morning hours, DHEAS levels show no diurnal variation. From a practical point of view, measurement of DHEAS is preferable to DHEA, as levels are more stable. Production Production of DHEA from Cholesterol Production of DHEA from Cholesterol DHEA is produced from cholesterol through two cytochrome P450 enzymes. Cholesterol is converted to pregnenolone by the enzyme P450 scc side chain cleavage; then another enzyme, CYP17A1, converts pregnenolone to 17α-Hydroxypregnenolone and then to DHEA. In humans, DHEA is the dominant steroid hormone and precursor of all sex steroids. Role DHEA can be understood as a prohormone for the sex steroids. DHEAS may be viewed as buffer and reservoir. As most DHEA is produced by the zona reticularis of the adrenal, it is argued that there is a role in the immune and stress response.who? As almost all DHEA is derived from the adrenal glands, blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have elevated levels of DHEAS. Effects and uses Studies have shown that DHEA is useful in patients with systemic lupus erythematosus. An application of the evidence was discussed by the U.S. Food and Drug Administration in 2001 and is available online.2 This review also shows that cholesterol and other serum lipids decrease with the use of DHEA mainly a decrease in HDL-C and triglycerides can be expected in women, p110. DHEA supplementation has been studied as a treatment for Alzheimer's disease, but was found to be ineffective.3 Some small placebo-controlled randomized clinical trial studies have found long-term supplementation to improve mood and relieve depression45 or to decrease insulin resistance.6 However, a larger placebo-controlled randomized clinical trial reported in the New England Journal of Medicine in 2006 found that DHEA supplementation in elderly men and women had no beneficial effects on body composition, physical performance, insulin sensitivity, or quality of life.7 In contrast to the non-beneficial effects of DHEA on memory in the elderly, a randomised UK study8 found that a 7-day course of DHEA 150 mg twice daily improved episodic memory in healthy young men. In this study, DHEA was also shown to improve subjective mood and decrease evening cortisol concentration, which is known to be elevated in depression9. The effect of DHEA on memory appeared to be related to an early activation of the anterior cingulate cortex ACC and it was suggested this was due to neuronal recruitment of the steroid sensitive ACC that may be involved in pre-hippocampal memory processing. DHEA supplements are sometimes used as muscle-building or performance-enhancing drugs by athletes. However, a randomized placebo-controlled trial found that DHEA supplementation had no effect on lean body mass, strength, or testosterone levels.10 A 1986 study found that a higher level of endogenous DHEA, as determined by a single measurement, correlated with a lower risk of death or cardiovascular disease.11 However, a more recent 2006 study found no correlation between DHEA levels and risk of cardiovascular disease or death in men.12 A 2007 study found the DHEA restored oxidative balance in diabetic patients, reducing tissue levels of pentosidine-a biomarker for advanced glycation endproducts.13 Some in vitro studies have found DHEA to have an anti-proliferative or apoptotic effect on cancer cell lines.141516 The clinical significance of these findings, if any, is unknown. Higher levels of DHEA, in fact, have been correlated with an increased risk of developing breast cancer in both pre- and postmenopausal women.1718 An anonymous 2002 review, in the French journal Prescrire, concluded: DHEA plasma levels are so low in most animals that they are difficult to measure, hindering studies on DHEA and aging. DHEA had not yet, at the time of writing, been linked to any specific health disorder. Side effects are liked to its androgenic effects, unfavorable lipid metabolism effects, and possible growth-stimulating effect on hormone dependent malignancies. In practice, there is currently no scientific reason to prescribe DHEA for any purpose whatsoever.19 A 2005 study, measured serum DHEA in 206 men with type-2 diabetes, and found an inverse relationship between serum DHEA and carotid atherosclerosis in men. The authors say the study supports the notion that DHEA, which is sold in increasing amount as a food supplement, is atheroprotective in humans, and that androgen replacement therapy should be considered for men with hypogonadism.20 A 2006 study supplemented DHEA to men of average 65 years of age, and found that the men experienced significant increases in testosterone and cGMP Cyclic guanosine monophosphate, and significant decreases in low-density liprotein LDL. The authors say that the findings...suggest that chronic DHEA supplementation would exert antiatherogenic effects, particularly in elderly subjects who display low ciriculating levels of this hormone.21 A 2008 study in the Journal of the American Geriatrics Society, June 2008, measured serum DHEA in 940 men and women ranging from age 21 to 88, following them from 1978 until 2005. The researches found that low levels of DHEA-s showed a significant association with shorter lifespan and that higher DHEA-s levels are a strong predictor of longevity in men, even after adjusting for age, blood pressure, and plasma glucose. No relationship was found between serum DHEA and longevity for women during the study period. The study did not find a signigicant difference in longevity until the 15-year follow-up point, which the researchers note may explain why some past research that followed men for less duration found no relationship.22 Disputed effects In the United States, DHEA or DHEAS have been advertised with claims that they may be beneficial for a wide variety of ailments. DHEA and DHEAS are readily available in the United States, where they are marketed as over-the-counter dietary supplements.23 A 2004 review in the American Journal of Sports Medicine concluded that The marketing of this supplement's effectiveness far exceeds its science.24 Because DHEA is converted to androstenedione and then testosterone, it has two chances to aromatize into estrogen- estrone from androstenedione, and estradiol from testosterone. As such, it is possible for increases in estrogen levels more than testosterone in men. Increasing endogenous production Regular exercise is known to increase DHEA production in the body.252627 Caloric restriction has also been shown to increase DHEA in primates.28 Some theorize that the increase in endogenous DHEA brought about by caloric restriction is partially responsible for the longer life expectancy known to be associated with caloric restriction.29 Legality United States A bill has been introduced, in March 2007, in the U.S. Senate S. 762 that attempts to classify DHEA as a controlled substance under the category of anabolic steroids. The sponsor is Charles Grassley R-IA. The cosponsors are Richard Durbin D-IL, and John McCain R-AZ.30 This bill was referred to the Senate Judiciary Committee. Then in December 2007, Charles Grassley introduced the S. 2470: Dehydroepiandrosterone Abuse Reduction Act of 2007, in an attempt to amend the Controlled Substances Act to make unlawful for any person to knowingly selling, causing another to sell, or conspiring to sell a product containing dehydroepiandrosterone to an individual under the age of 18 years, including any such sale using the Internet, without a prescription. The bill was read twice and referred to the Senate Judiciary Committee.31 Canada In Canada, a prescription is required to buy DHEA.32 References ^ Romieu, P., Martin-Fardon, R., Bowen, W. D., Maurice, T. 2003. Sigma 1 Receptor-Related Neuroactive Steroids Modulate Cocaine-Induced Reward. 239: 3572. ^ FDA document regading DHEA and SLE ^ Wolkowitz OM, Kramer JH, Reus VI, et al 2003. DHEA treatment of Alzheimer's disease: a randomized, double-blind, placebo-controlled study. Neurology 60 7: 1071-6. PMID 12682308. ^ Wolkowitz OM, Reus VI, Keebler A, et al 1999. Double-blind treatment of major depression with dehydroepiandrosterone. The American journal of psychiatry 156 4: 646-9. PMID 10200751. ^ Schmidt PJ, Daly RC, Bloch M, et al 2005. Dehydroepiandrosterone monotherapy in midlife-onset major and minor depression. Arch. Gen. Psychiatry 62 2: 154-62. doi:10.1001/archpsyc.62.2.154. PMID 15699292. ^ Kawano H, Yasue H, Kitagawa A, et al 2003. Dehydroepiandrosterone supplementation improves endothelial function and insulin sensitivity in men. J. Clin. Endocrinol. Metab. 88 7: 3190-5. PMID 12843164. ^ Nair KS, Rizza RA, O'Brien P, et al 2006. DHEA in elderly women and DHEA or testosterone in elderly men. N. Engl. J. Med. 355 16: 1647-59. doi:10.1056/NEJMoa054629. PMID 17050889. ^ Alhaj et al Effects of DHEA administration on episodic memory, cortisol and mood in healthy young men: a double-blind, placebo-controlled study, Psychopharmacology 2006 188: 541-551 ^ Young EA, Haskett RF, Grunhaus L, Pande A, Weinberg VM, Watson SJ, Akil H 1994 Increased evening activation of the hypothalamic-pituitary-adrenal axis in depressed patients. Arch Gen Psychiatry 51:701-707 ^ Wallace MB, Lim J, Cutler A, Bucci L 1999. Effects of dehydroepiandrosterone vs androstenedione supplementation in men. Medicine and science in sports and exercise 31 12: 1788-92. PMID 10613429. ^ Barrett-Connor E, Khaw KT, Yen SS 1986. A prospective study of dehydroepiandrosterone sulfate, mortality, and cardiovascular disease. N. Engl. J. Med. 315 24: 1519-24. PMID 2946952. ^ Arnlöv J, Pencina MJ, Amin S, et al 2006. Endogenous sex hormones and cardiovascular disease incidence in men. Ann. Intern. Med. 145 3: 176-84. PMID 16880459. ^ Will Boggs. DHEA Restores Oxidative Balance in Type 2 Diabetes. Medscape. Retrieved on 2007-12-14. ^ Yang NC, Jeng KC, Ho WM, Hu ML 2002. ATP depletion is an important factor in DHEA-induced growth inhibition and apoptosis in BV-2 cells. Life Sci. 70 17: 1979-88. PMID 12148690. ^ Schulz S, Klann RC, Schönfeld S, Nyce JW 1992. Mechanisms of cell growth inhibition and cell cycle arrest in human colonic adenocarcinoma cells by dehydroepiandrosterone: role of isoprenoid biosynthesis. Cancer Res. 52 5: 1372-6. PMID 1531325. ^ Loria RM 2002. Immune up-regulation and tumor apoptosis by androstene steroids. Steroids 67 12: 953-66. PMID 12398992. ^ Tworoger SS, Missmer SA, Eliassen AH, et al 2006. The association of plasma DHEA and DHEA sulfate with breast cancer risk in predominantly premenopausal women. Cancer Epidemiol. Biomarkers Prev. 15 5: 967-71. doi:10.1158/1055-9965.EPI-05-0976. PMID 16702378. ^ Key T, Appleby P, Barnes I, Reeves G 2002. Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies. J. Natl. Cancer Inst. 94 8: 606-16. PMID 11959894. ^ DHEA: the last elixir 2002. Prescrire international 11 60: 118-23. PMID 12199273. ^ M . Fukui , Y . Kitagawa , N . Nakamura , M . Kadono , M . Yoshida , C . Hirata , K . Wada , G . Hasegawa , T . Yoshikawa 2005. Serum dehydroepiandrosterone sulfate concentration and carotid atherosclerosis in men with type 2 diabetes. Atherosclerosis Volume 181 2: 339-344. ^ Martina V, Benso A, Gigliardi VR, et al. 2006. Short-term dehydroepiandrosterone tereatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol Oxf. 11 March;643: 260-4. ^ Enomoto, Mika MD, PhD 2008. Serum Dehydroepiandrosterone Sulfate Levels Predict Longevity in Men: 27-Year Follow-Up Study in a Community-Based Cohort Tanushimaru Study.. Journal of the American Geriatrics Society 56 6. ^ Calfee R, Fadale P March 2006. Popular ergogenic drugs and supplements in young athletes. Pediatrics 117 3: e577-89. doi:10.1542/peds.2005-1429. PMID 16510635. In 2004, a new Steroid Control Act that placed androstenedione under Schedule III of controlled substances effective January 2005 was signed. DHEA was not included in this act and remains an over-the-counter nutritional supplement. ^ Tokish JM, Kocher MS, Hawkins RJ 2004. Ergogenic aids: a review of basic science, performance, side effects, and status in sports. The American journal of sports medicine 32 6: 1543-53. doi:10.1177/0363546504268041. PMID 15310585. ^ Eur J Appl Physiol Occup Physiol 1998 Oct;785:466-71 ^ Eur J Appl Physiol. 2001 Jul;851- 2:177-84 ^ J Gerontol A Biol Sci Med Sci. 2002 Apr;574:B158-65 ^ Exp Gerontol. 2003 Jan-Feb; 381-2:35-46 ^ Roberts E. The importance of dehydroepiandrosterone sulfate in the blood of primates: a longer and healthier life? Biochem Pharmacol. 1999 Feb 15;574:329-46. ^ S. 762: A bill to include dehydroepiandrosterone as an anabolic steroid, from Govtrack.us. Accessed May 9, 2007. ^ S. 2470: Dehydroepiandrosterone Abuse Reduction Act of 2007 GovTrack.us ^ Dr. Michael Colgin. The Deal With D.H.E.A. Vista Magazine Online. www.vistamag.com 1 External links Information on DHEA from the Mayo Clinic Information on DHEA from the American Cancer Society DHEA in elderly women and DHEA or testosterone in elderly men, published in the New England Journal of Medicine in 2006. Neither DHEA nor low-dose testosterone replacement in elderly people has physiologically relevant beneficial effects on body composition, physical performance, insulin sensitivity, or quality of life. DHEA, from the Skeptic's Dictionary v d e Anabolic steroids A14 tradename in brackets Androstan carbon 19 present Androstadienone Boldenone undecylenate Equipoise 4-Chlordehydromethyltestosterone Turinabol Clostebol Desoxymethyltestosterone Madol DHEA DHT Drostanolone Masteron Fluoxymesterone Halotestin Furazabol Miotolan Methandrostenolone Dianabol Methenolone Methenolone enanthate Primobolan Mesterolone Proviron Mestanolone Norethandrolone Oxandrolone Anavar Oxymetholone Anadrol Oxymetholone Anadrol-50 Quinbolone Anabolicum Vister Stanozolol Winstrol Testosterone Estren carbon 19 absent Ethylestrenol Mibolerone Cheque Drops Metribolone R1881 Nandrolone Deca Durabolin Norbolethone Genabol Oxabolone cipionate Tetrahydrogestrinone The Clear Trenbolone Fina Retrieved from http://en..org/wiki/Dehydroepiandrosterone Categories: Androgens | Neurosteroids | Dietary supplementsHidden category: Articles with specifically-marked weasel-worded phrases Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français עברית Nederlands 日本語 Norsk bokmål Polski Português Svenska This page was last modified on 2 September 2008, at 18:24
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